CN106146796A - Urethanes dispersant - Google Patents
Urethanes dispersant Download PDFInfo
- Publication number
- CN106146796A CN106146796A CN201510144172.0A CN201510144172A CN106146796A CN 106146796 A CN106146796 A CN 106146796A CN 201510144172 A CN201510144172 A CN 201510144172A CN 106146796 A CN106146796 A CN 106146796A
- Authority
- CN
- China
- Prior art keywords
- dispersant
- compound
- independently selected
- diisocyanate
- isocyanate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 73
- 150000003673 urethanes Chemical class 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 25
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 25
- 239000000049 pigment Substances 0.000 claims abstract description 22
- 229920000768 polyamine Polymers 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000001412 amines Chemical class 0.000 claims abstract description 17
- -1 Urethane ester Chemical class 0.000 claims abstract description 14
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000006185 dispersion Substances 0.000 claims abstract description 10
- 239000012634 fragment Substances 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 53
- 239000012948 isocyanate Substances 0.000 claims description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 150000002513 isocyanates Chemical class 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 18
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 10
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 10
- 239000013638 trimer Substances 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 9
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical class NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 7
- 125000005442 diisocyanate group Chemical group 0.000 claims description 7
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 7
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 5
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 5
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 4
- 239000012860 organic pigment Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- 150000007824 aliphatic compounds Chemical class 0.000 claims description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000001023 inorganic pigment Substances 0.000 claims description 3
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 claims description 3
- 229960001124 trientine Drugs 0.000 claims description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001334 alicyclic compounds Chemical class 0.000 claims description 2
- 150000002466 imines Chemical class 0.000 claims description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 2
- 229920000083 poly(allylamine) Polymers 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 claims 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- QVTVDJWJGGEOGX-UHFFFAOYSA-N urea;cyanide Chemical compound N#[C-].NC(N)=O QVTVDJWJGGEOGX-UHFFFAOYSA-N 0.000 claims 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 150000005217 methyl ethers Chemical class 0.000 description 15
- 239000000376 reactant Substances 0.000 description 12
- 238000012544 monitoring process Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000004448 titration Methods 0.000 description 11
- 229920001223 polyethylene glycol Polymers 0.000 description 10
- 239000004814 polyurethane Substances 0.000 description 10
- 229920002635 polyurethane Polymers 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000009736 wetting Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 239000004202 carbamide Chemical group 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 4
- 230000003381 solubilizing effect Effects 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000005352 clarification Methods 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003141 primary amines Chemical group 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 1
- QKOWXXDOHMJOMQ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)biuret Chemical compound O=C=NCCCCCCNC(=O)N(CCCCCCN=C=O)C(=O)NCCCCCCN=C=O QKOWXXDOHMJOMQ-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 1
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- KIBKSNLNGHPFTB-UHFFFAOYSA-L [acetyloxy(diethyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CC[Sn+2]CC KIBKSNLNGHPFTB-UHFFFAOYSA-L 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 150000001261 hydroxy acids Chemical group 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 150000002527 isonitriles Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3228—Polyamines acyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6685—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/009—Non common dispersing agents polymeric dispersing agent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/004—Pigment pastes, e.g. for mixing in paints containing an inorganic pigment
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- Chemical Kinetics & Catalysis (AREA)
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- Materials Engineering (AREA)
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Abstract
Urethane ester type dispersant, it includes derived from following fragment: (1) one or more there is the polyisocyanate of at least 2.0 isocyanate groups, (2) have the monofunctional compound of isocyanate-reactive functional moiety；And (3) amine degree of functionality is two or more polyamine.This dispersant can be prepared in the most solvent-laden preparation process.This dispersant can apply in water-based pigment dispersions system.
Description
Invention field
Present disclosure describes the dispersant based on urethanes and urea bond, it is in polarity
Medium such as abrasive, coating and ink disperse organic/inorganic pigment granules.Specifically, this point
Powder packets contains effective multiple anchor portions with amide, urea and urethane groups,
Its integrated distribution is connected in dispersant molecule and with the solvent making chain structure solubilising.
More specifically, chemical constitution mentioned above is suitable to prepare condensed pigment, it is further adapted for steady
Determine binding agent, coating, ink composite, plastics and polymeric blends.As wetting and dispersing
Agent, they reduce the viscosity of this system, improve storage stability and fluid properties, and also can
To strengthen intensity of colour.
Background
Multiple different urethanes or polyurethane dispersant contain polyethylene oxide chain, should
Chain is present in the side chain being connected with polyurethane skeleton and/or end chain and multi-functional anchor of arranging in pairs or groups
Determine group.
WO97/19120 considers water dispersible unsaturated polyurethanes dispersant, and it includes hanging
Unsaturated alkyl group, the sulfonate of pendency and the polyalkylene oxide hung down.It discloses polyurethane to fit
In stable aqueous dispersion and the pigment dispersion of preparing hydrophobic polymer.
2009/0221745A1 United States Patent (USP) describes based on polyepoxide main chain poly-
Epoxy/amine type dispersant, this main chain has as anchor with little with what surface of pigments interacted
Amine molecule (benzylamine or ethanolamine) and as solubilising tail (solubilizing tail) with in a solvent
(trade mark, from HUNTSMAN's for the polyetheramine extended) and binding agent Jie
Matter is to provide stabiliser.This wetting dispersing agent can be high with general binding agent and dicyandiamide solution
Spend compatible.
Other are also had to be in progress in this field.8017686B2 United States Patent (USP) mentions novel poly-ammonia
Ester dispersant binder, it has the side base containing hydrophilic and hydrophobic polyalkylene oxide based on pendency
Polyurethane skeleton.The content of the polyalkylene oxide in polyurethane dispersant resin is at least 45%.
This document describing condensed pigment to can be easy to be incorporated in coating composition, pigment solids is stably
It is dispersed therein.Additionally, dispersant resin can be applicable to and the different pigment one in the range of wide spectrum
Rise use, especially for being difficult to scattered tricky cases, as DPP red BO (Ciba),
Heliogene Blue L7101F (BASF) and Quindo Violet RV929 (Bayer).
8664331B2 United States Patent (USP) also discloses a class polyurethane dispersant, and it contains
In side chain, the substantial amounts of oxirane of 35wt% to 90wt% based on total polymer weight repeats single
Unit.Hydroxy-acid group as anchor portion is merged in polyurethane skeleton.For graining paste or painting
Feed composition, the dispersant of these excellences can provide the functional character of improvement, such as abrasive
Viscosity, glossiness and intensity of colour.
Therefore, above-mentioned dispersant obtains many excellent performance, water-dispersible and binding agent
System and the extensive compatibility of various pigment, the lower viscosity of abrasive and dispersion
Long-time stability.But up to now, at urethanes or polyurethane-type dispersant
Building-up process exists organic solvent always, and this will likely result in the problem of crosslinking, if
Relate to the anchoring group of the multi-functional excellence of such as polyamine derivatives.Therefore, at wettability
With between environmental friendliness problem, there is breach in urethanes or polyurethane-type dispersant.
Polyacrylic acid (PAA), sodium polyacrylate (NaPAA) and related derivatives are the 3945843rd
A United States Patent (USP) is disclosed, and 4767644A United States Patent (USP) has for not containing
The another kind of method of the dispersant of organic solvent.But the profit of dispersant this kind of for organic pigment
Wet ability is the most defective, and this is owing to polarity is not mated.Therefore, it is always lived with class surface
Property agent dispersant package is to strengthen wetting effect.
This makes more to be difficult to ignore volatile organic matter problem.Environmental friendliness problem not only limits
The application of dispersant and limit its production process.From urethanes or polyurethanes
From the perspective of the building-up process of dispersant, relate to a large amount of organic solvent: ester, example the most always
Such as butyl acetate and Methoxypropylacetate；Amide, such as dimethylformamide；Lactams,
Such as METHYLPYRROLIDONE；Or ketone, such as methyl ethyl ketone (MEK) and methyl-isobutyl
Ketone (MIBK).On the other hand, the wettability of dispersant is paid high attention to, particularly with high table
The situation of face energy, such as water-based paint compositions.Therefore, eco-friendly production process with
Breach is there is between the pigment wetting performance of dispersant.
Summary of the invention
In one embodiment, the disclosure provides dispersant, and it includes derived from following sheet
Section: (1) one or more there is the polyisocyanate of at least 2 isocyanate groups, (2) have
There is the monofunctional compound of isocyanate-reactive functional moiety；And (3) amine degree of functionality be two or
More polyamine.In some embodiments, dispersant is water miscible.
In some embodiments, the isocyanate groups of the polyisocyanate of 50%-90% equivalent
Be combined with monofunctional compound, and the isocyanate groups of 10%-50% equivalent is tied with polyamine
Close.
In some embodiments, monofunctional compound is independently selected from aliphatic compound, fat
Ring compounds of group and aromatic compound, and combinations thereof.In some embodiments, simple function
Compound contains at least one independently selected from following group :-O-or-COO-and combinations thereof.
In some instances, the molecular weight of monofunctional compound is 350 to 5000.Some embodiment party
In case, monofunctional compound is independently selected from the poly-(C containing 60%-99% ethylene oxide group2-4-
Alkylene oxide), polyester oligomer, and combinations thereof.In some of such embodiment, polyester oligomeric
Thing contains the fragment derived from dicarboxylic acids and ethylene glycol.
In some embodiments, polyisocyanate is diisocyanate, and it is independently selected from first
Phenylene diisocyanate, isophorone diisocyanate (IPDI), hexamethylene diisocyanate,
Double (the 2-of diphenyl-methane-4,4'-diisocyanate, dicyclohexyl methyl hydride-4,4'-diisocyanate, 1,4-
Isocyano (isocyanato)-2-base) benzene, trimethyl hexamethylene diisocyanate, or these two
The mixture of isocyanates.In some of the other embodiments, polyisocyanate independently selected from
Adduct, isocyanates biuret, isocyanates isocyanuric acid ester or this kind of polyisocyanate
Mixture.In certain embodiments, polyisocyanate is independently selected from toluene di-isocyanate(TDI)
With trimethylolpropane adduct, hexamethylene diisocyanate biruet trimer, six methylenes
Group diisocyanate isocyanurate trimer, isophorone diisocyanate isocyanuric acid ester three
Aggressiveness, hexamethylene diisocyanate isocyanurate trimer, and isophorone diisocyanate
Ester isocyanurate trimer.
In some embodiments, isocyanate-reactive functional moiety independently selected from hydroxyl,
Amine or imines and combinations thereof.
In some embodiments, polyamine independently selected from polymine (PEI), polyvinylamine,
Polyallyl amine oligomer, aziridine oligomer and combinations thereof.In some embodiments,
Polyamine is independently selected from diethylenetriamines (DETA), trien (TETA), four sub-second
Base five amine (TEPA), penten (PEHA), six ethylidene seven amine (HEHA) and groups thereof
Close.
Embodiment describes in detail
The present invention provides the dispersant composition with end solubilizing group, and it is by without solvent
Building-up process obtain via urethanes and urea bond.It may be used for water based paint and molten
Agent base coating.Meanwhile, this dispersant composition can provide the moistening effect of excellence to obtain tool
There are extremely low viscosity and the mill base of good long-term colloidal stability.It includes as dispersant
Anchor portion with absorption polyamine on the surface of the pigment, and monohydroxy compound end-blocking is poly-different
Cyanate, to form isocyanates list adduct as solvent solubilizing group, in polyisocyanate
Only retain a degree of functionality.
In one embodiment, the disclosure provides dispersant, and it has derived from following sheet
Section: (1) one or more there is the polyisocyanate of at least 2 isocyanate groups, (2) have
The monofunctional compound of isocyanate-reactive functional moiety；And (3) amine degree of functionality is two or more
Many polyamine.
In another embodiment, dispersant can obtain from the reaction not containing machine solvent:
(1) one or more have the polyisocyanate of at least 2 isocyanate groups, have different with (2)
The monofunctional compound of polyisocyanate reactant functional moiety is reacted to form in isocyanates list adduction
Mesosome.Isocyanates list adduction intermediate is that two or more polyamine are anti-subsequently with (3) amine degree of functionality
Should.
According to dispersant composition as herein described, component (1) can be to have at least 2 isocyanides
The polyisocyanate of acid esters group.In one embodiment, polyisocyanate includes aliphatic
Isocyanates, alicyclic isocyanate, aromatic isocyanate, heterocyclic isocyanate, and
Mixture.In some embodiments, the number of the isocyanate groups of this kind of polyisocyanate
Can be 2 to 8,2 to 5, or 2 to 4.In other embodiments, isocyanate groups
Average be 2 to 5.Have two isocyanate functional groups polyisocyanate be suitable for
Example is diisocyanate, such as toluene di-isocyanate(TDI) (TDI, 80/20), isophorone two
Isocyanates (IPDI), hexamethylene diisocyanate (HDI), diphenyl-methane-4,4'-two Carbimide.
Double (the 2-isocyanide of ester (4,4'-MDI), dicyclohexyl methyl hydride-4,4'-diisocyanate (HMDI), 1,4-
Acid group-2-base) benzene (TXMDI), trimethyl hexamethylene diisocyanate (" TMDI "), or these
The mixture of diisocyanate.In one embodiment, polyisocyanate be TDI, IPDI,
HMDI, and its mixture.In one embodiment, polyisocyanate is TDI.One
In individual embodiment, polyisocyanate includes HDI isocyanurate trimer, and IPDI
Isocyanurate trimer.Multi-functional example is the addition by diisocyanate and polyhydric alcohol
The Desmodur L that product obtains, and the Desmour N obtained by biuret reaction, different by two
The Desmodur IL that cyanate cyclisation obtains.
Further according to dispersant composition specifically described herein, component (2) can be to have isocyanide
The monofunctional compound of acid esters reactive functional part.In one embodiment, monofunctional
Compound can be the molecular weight with 350g/mole to 5000g/mole aliphatic compound,
Alicyclic compound, aromatic compound, and combinations thereof, and can be contained one or more
Ehter bond, ester bond and mixture thereof.In some embodiments, this kind of monofunctional compound point
Son amount can be: 550g/mole to 3000g/mole；550g/mole to 2000g/mole or
550g/mole to 1000g/mole.The isocyanates reaction of the embodiment of monofunctional compound
Functional moiety is independently selected from hydroxyl, amino or imino group and combinations thereof for property.
In one embodiment, monofunctional compound can be monohydroxy compound.At one
In embodiment, monohydroxy compound can be linear, branched, and mixture.?
In some of the other embodiments, monohydroxy compound can be saturated or unsaturated.At certain
In a little embodiments, monohydroxy compound is saturated.
In a certain embodiment, monofunctional compound includes poly-(C2-4-alkylene oxide) compound.Can
That take is poly-(C2-4-alkylene oxide) compound have low-molecular-weight make its effectively act as point
The effect of the solubilizing group of powder.In some embodiments, in final and dispersant structure
Number-average molecular weight Mn of the polyalkylene oxide chain that anchor portion is connected is 350g/mole to 5000
g/mole；Or 350g/mole to 3000g/mole or 350g/mole to 2000g/mole.
In one embodiment, poly-(C2-4-alkylene oxide) number-average molecular weight of compound is less than 5000
g/mole.In another embodiment, poly-(C2-4-alkylene oxide) compound number-average molecular weight not
More than 3000g/mole.In still another embodiment, poly-(C2-4-alkylene oxide) number of compound
Average molecular weight is less than 2000g/mole.In this kind of embodiment, poly-(C2-4-alkylene oxide) change
The number-average molecular weight of compound is at least 350g/mole.
In another embodiment, monofunctional compound can be polyester oligomer.Polyester is low
Polymers can be obtained by known technology, such as one or more dicarboxylic acids, ethylene glycol, anhydride,
Hydroxy carboxylic acid and can apply to the polycondensation reaction of other material any of esterification.Or,
The ring-opening polymerisation of the corresponding lactone of such as δ-valerolactone and/or 6-caprolactone is also suitably to select.
In one embodiment, monofunctional compound and component (1) are reacted to form isocyanates
Single adduction intermediate.In one embodiment, there is the poly-of at least 2 isocyanate groups
Isocyanates has a structure of formula (1):
Wherein Q is aliphatic group, aromatic group, aralkyl or optionally by hetero atom, amide groups,
The fat that ester group, carbamate groups, carbonate group, urea groups or a combination thereof one or many interrupt
Race's main chain or aromatic backbone；X be direct key, alkylidene, alkenylene, alkynylene, arlydene,
Cycloalkylidene, sub-Heterocyclylalkyl, inferior heteroaryl, cycloalkyl-alkylidene, arylene-alkylene,
Cycloalkylidene-arlydene, sub-heterocycloalkyl-alkyl, inferior heteroaryl-alkylidene；And
R is the integer of 2 to 8.
In at least one embodiment, the isocyanates list adduction intermediate of formula (2) is to pass through
The reaction of the monofunctional compound of Y-Z form and component (1) is formed:
Wherein, the Z of compound Y-Z is nucleophilic group；Y is aliphatic group, alicyclic group, virtue
Race's base or a combination thereof, the molecular weight of compound Y-Z be 350g/mole to 5000g/mole or
350g/mole to 3000g/mole or 350g/mole to 2000g/mole, and can contain
There are one or more ehter bonds, ester bond or its mixture；P is the equivalents of compound Y-Z；r
For the equivalents of NCO group in polyisocyanate:
Q has identical implication presented above；And (r-p) it is unreacted NCO group
Equivalents.The reaction of the monofunctional compound of Y-Z form and component (1) can be by scheme 1 table
Show:
Scheme 1
In another embodiment, the monofunctional compound of Y-Z form and component (1) react with
The isocyanates list adduction midbody product of formation formula (3):
Wherein (r-1) is that (every polyisocyanate is divided for the equivalents of the NCO reacted with compound Y-Z
Son), and the equivalents that (r-1) is the Y-Z reacted with component (1)；Y, Z, Q, r and X are
Just like the identical implication defined in formula (1).The monofunctional compound of Y-Z form and component (1)
Reaction can be represented by scheme 2:
Scheme 2
In at least one preferred embodiment, compound Y-Z is monohydroxy compound,
Y-OH, it forms the isocyanates list adduction intermediate of formula (3.1) with component (1) when reacting
Product:
Wherein (r-1) is equivalents (every polyisocyanate of the NCO reacted with compound Y-OH
Molecule)；Y, Q, r with X all just like the identical implication defined in formula (1).Monohydroxylated
Compound Y-OH can be represented by scheme 3 with the reaction of component (1):
Scheme 3
Some sides of being preferable to carry out at the isocyanates list adduction midbody product of formula (2) and formula (3)
In case, Z is-O-,--or-NR-, wherein R can be that to have 1 to 10 carbon former to NH
Alkyl, cycloalkyl, aryl or a combination thereof of son.At least one enforcement at the compound of formula (1)
In scheme, Q derived from biuret (imino-diacetic carbamide) or 1,3,5-triazines-2,4,6-tri-
Ketone or a combination thereof.
Further according to dispersant composition as herein described, component (3) can be that amine degree of functionality is
Two or more polyamine.In such embodiment, polyamine includes poly-(C2-6-alkylidene
Imines), such as polymine (PEI) and for the polyvinylamine of C2 compound, for C3ization
The PAH of compound.In some embodiments, polyamine can be linear or branched.
Exemplary aliphatic linear polyamine includes primary amine groups and secondary amine, such as diethylenetriamines
(DETA), trien (TETA), tetren (TEPA), five ethylidene six
Amine (PEHA), six ethylidene seven amine (HEHA) and similar senior analog.Exemplary fat
Race's branched polyamines include primary amine groups, secondary amine and tertiary amine groups and its have 600 to 30000 or
Number-average molecular weight Mn of the polyamine of 1000 to 10000.Exemplary polymine includes line
Property polymine or branched polyethylene imine.Commercial polyethylene imines is with BASF'sAnd Nippon ShokubaiSell.
In one embodiment, dispersant composition is water miscible.
In one embodiment, dispersant composition can be in the condition not using organic solvent
Lower preparation, thus VOC will not be discharged in course of reaction.Therefore, exist
Initial reaction stage should be noted that heat history phenomenon.The custom catalysts preparing polyurethane can be used in heat
Reaction rate is accelerated, such as tin catalyst after release.For example, it is possible to from NITTO KASEI
Obtain dibutyl tin laurate, dibutyltin diacetate and diethyltin diacetate.All right
Application bismuth catalyst, such as commercial compound, the K-of KING INDUSTRIES company
Series of products or NITTO KASEI companySeries of products.
Isocyanates list adduction intermediate is carried out by known method with the reaction of component (3).
Generally, urea bond is formed during these, and reaction is often used without extra catalyst and organic
Solvent.In some embodiments, based on poly-(C2-6-alkylene imine) framework molecular structure will
Cause starlike geometry.Isocyanates list adduction intermediate as solubilising moieties will be at end
Position is connected with anchor frame.
Dispersive process has three Main Stage, pigment wetting, pigment disintegrate and pigment stabilizer.
Wet processes, this process by surface of pigments state from solid/gas surface conversion to solid-liquid interface.In order to
Pigment solids being introduced in liquid medium, high shear force is required.Thus it is common to use point
Powder is to reduce these dispersion forces and thus to be inputted and jitter time by the gross energy needed for system
All minimize.Additionally, dispersant also provides for stabiliser to prevent from reuniting again.Known dispersion
Agent is usually surfactant, it only directly applies to solid on a small quantity or adds liquid medium
In.Disperse medium homogenizing after pigment agglomerate is the most deflocculated, can after scatter operation
Situation about reuniting again with generation.In that way it is possible to generation counter productive, such as viscosity in liquid system
Increase, loose colour and grow dim, or the loss of the gloss of ink and coating.
The compounds of this invention is used as organic or inorganic pigment or the wetting dispersing agent of filler.Its use
Amount is for based on the 0.5wt% to 50wt% treating dispersing solid in ink and coating composition.So
And, for needing more substantial dispersant during high surface of pigments under dispersion condition.
Embodiment
Following example further describe and represent exemplary embodiment party within the scope of the present invention
Case.Embodiment is provided to be merely cited for and be not interpreted as limitation of the present invention, because of
For in the case of without departing from the spirit and scope of the present invention, multiple change is possible.
Embodiment 1
Tri-mouthfuls of reaction flasks of 1000mL are equipped with thermometer, reflux condenser, heating mantle and machine
50.0 parts of toluene di-isocyanate(TDI)s (TDI) are put in reaction vessel and at nitrogen by tool agitator
And stirred at ambient temperature.287.0 parts of PEG methyl ethers (DME-1000) are passed through dropping liquid
Funnel was added dropwise in reactor with 1.5 hours.Reactant mixture is heated to 70 DEG C, and
And according to the DIN 53185 reduction by titrimetry monitoring NCO%.When NCO% is down to
When 3.6%, 9.9 parts of diethylenetriamines (DETA) were added dropwise over 1 hour.By mixture
It is heated to 85 DEG C and is stirred for 3 hours at such a temperature.Remove thermal source.By 520.4 parts of water
Join in the mixture of heat.Product be solid content be the clear light yellow solution of 40.3%.This
It it is dispersant 1.
Embodiment 2
Similar to Example 1,50.0 parts of toluene di-isocyanate(TDI)s (TDI) are put into reaction vessel
In and at nitrogen and stirred at ambient temperature.By 287.0 parts of PEG methyl ethers
(DME-1000) it is added dropwise in reactor with the time of 1.5 hours by Dropping funnel.Will
Reactant mixture is heated to 70 DEG C, and by the reduction of titrimetry monitoring NCO%.When
When NCO% is down to 3.6%, by 10.5 parts of triens (TETA) with time of 1 hour
It is added dropwise over.Heat the mixture to 85 DEG C and be stirred for 3 hours at such a temperature.Remove
Thermal source.521.3 parts of water are joined in the mixture of heat.Product be solid content be 39.7% clear
Light yellow solution.This is dispersant 2.
Embodiment 3
Similar to Example 1,50.0 parts of toluene di-isocyanate(TDI)s (TDI) are put into reaction vessel
In and at nitrogen and stirred at ambient temperature.By 287.0 parts of PEG methyl ethers
(DME-1000) it is added dropwise in reactor with the time of 1.5 hours by Dropping funnel.Will
Reactant mixture is heated to 70 DEG C, and by the reduction of titrimetry monitoring NCO%.When
When NCO% is down to 3.6%, 10.9 parts of tetrens (TEPA) were dropwise added with 1 hour
Enter.Heat the mixture to 85 DEG C and be stirred for 3 hours at such a temperature.Remove thermal source.
521.9 parts of water are joined in the mixture of heat.Product be solid content be 40.4% clarification yellowish
Color solution.This is dispersant 3.
Embodiment 4
By 60.0 parts of isophorone diisocyanate (IPDI) and 0.02 part of NEOSTANN
U-600 (being derived from NITTO KASEI CO., LTD) puts in reaction vessel, and at nitrogen
And stirred at ambient temperature.269.9 parts of PEG methyl ethers (DME-1000) are passed through dropping liquid
Funnel was added dropwise in reactor with the time of 1.5 hours.Reactant mixture is heated to
70 DEG C, and by the reduction of titrimetry monitoring NCO%.When NCO% is down to 3.4%,
9.3 parts of diethylenetriamines (DETA) were added dropwise over 1 hour.Heat the mixture to
85 DEG C and be stirred for 3 hours at such a temperature.Remove thermal source.508.8 parts of water are joined
In the mixture of heat.Product be solid content be the clear light yellow solution of 40.2%.This is dispersion
Agent 4.
Embodiment 5
Similar to Example 4, by 60.0 parts of isophorone diisocyanate (IPDI) and 0.02 part
NEOSTANN U-600 puts in reaction vessel, and at nitrogen and stirred at ambient temperature.
By 269.9 parts of PEG methyl ethers (DME-1000) by Dropping funnel with 1.5 hours time
Between be added dropwise in reactor.Reactant mixture is heated to 70 DEG C, and passes through titrimetry
The reduction of monitoring NCO%.When NCO% is down to 3.4%, by 9.9 parts of triens
(TETA) it is added dropwise over the time of 1 hour.Heat the mixture to 85 DEG C and in this temperature
3 hours it are stirred under degree.Remove thermal source.509.7 parts of water are joined in the mixture of heat.
Product be solid content be the clear light yellow solution of 40.0%.This is dispersant 5.
Embodiment 6
Similar to Example 4, by 60.0 parts of isophorone diisocyanate (IPDI) and 0.02 part
NEOSTANN U-600 puts in reaction vessel, and at nitrogen and stirred at ambient temperature.
By 269.9 parts of PEG methyl ethers (DME-1000) by Dropping funnel with 1.5 hours time
Between be added dropwise in reactor.Reactant mixture is heated to 70 DEG C, and passes through titrimetry
The reduction of monitoring NCO%.When NCO% is down to 3.4%, by 10.2 part of four ethylidene five
Amine (TEPA) was added dropwise over 1 hour.Heat the mixture to 85 DEG C and at such a temperature
It is stirred for 3 hours.Remove thermal source.510.2 parts of water are joined in the mixture of heat.Product
Be solid content be the clear light yellow solution of 39.6%.This is dispersant 6.
Embodiment 7
By 100 parts of isophorone diisocyanate (IPDI) and 0.02 part of NEOSTANN U-600
Put in reaction vessel, and at nitrogen and stirred at ambient temperature.By 247.4 parts of poly-(second two
Alcohol) methyl ether (MPEG-550) was added dropwise in reactor with 1.5 hours by Dropping funnel.
Reactant mixture is heated to 70 DEG C, and by the reduction of titrimetry monitoring NCO%.When
When NCO% is down to 5.4%, 15.5 parts of diethylenetriamines (DETA) were dropwise added with 1 hour
Enter.Heat the mixture to 85 DEG C and be stirred for 3 hours at such a temperature.Remove thermal source.
544.4 parts of water are joined in the mixture of heat.Product be solid content be 40.1% clarification yellowish
Color solution.This is dispersant 7.
Embodiment 8
Similar to Example 7, by 100 parts of isophorone diisocyanate (IPDI) and 0.02 part
NEOSTANN U-600 puts in reaction vessel, and at nitrogen and stirred at ambient temperature.
By 247.4 parts of PEG methyl ethers (MPEG-550) by Dropping funnel with 1.5 hours time
Between be added dropwise in reactor.Reactant mixture is heated to 70 DEG C, and passes through titrimetry
The reduction of monitoring NCO%.When NCO% is down to 5.4%, by 16.5 parts of triethylenes four
Amine (TETA) was added dropwise over the time of 1 hour.Heat the mixture to 85 DEG C and at this
At a temperature of be stirred for 3 hours.Remove thermal source.545.9 parts of water are joined in the mixture of heat.
Product be solid content be the clear light yellow solution of 40.5%.This is dispersant 8.
Embodiment 9
Similar to Example 7, by 100 parts of isophorone diisocyanate (IPDI) and 0.02 part
NEOSTANN U-600 puts in reaction vessel, and at nitrogen and stirred at ambient temperature.
By 247.4 parts of PEG methyl ethers (MPEG-550) by Dropping funnel with 1.5 hours time
Between be added dropwise in reactor.Reactant mixture is heated to 70 DEG C, and according to DIN 53185
Reduction by titrimetry monitoring NCO%.When NCO% is down to 5.4%, by 17.0 parts
Tetren (TEPA) was added dropwise over the time of 1 hour.Heat the mixture to 85 DEG C
And it is stirred for 3 hours at such a temperature.Remove thermal source.546.6 parts of water are joined heat
In mixture.Product be solid content be the clear light yellow solution of 40.2%.This is dispersant 9.
Embodiment 10
By 60 parts of Desmodur N 100 (Bayer, degree of functionality=3.8) and 0.02 part of NEOSTANN
U-600 puts in reaction vessel, and at nitrogen and stirred at ambient temperature.By 231.66 parts
PEG methyl ether (MPEG-1000) is dropwise added with the time of 1.5 hours by Dropping funnel
Enter to reactor.Reactant mixture is heated to 70 DEG C, and passes through according to DIN 53185
The reduction of titrimetry monitoring NCO%.When NCO% is down to 1.19%, sub-by 2.84 part two
Ethyl triamine (DETA) was added dropwise over the time of 1 hour.Heat the mixture to 85 DEG C also
And it is stirred for 3 hours at such a temperature.Remove thermal source.441.78 parts of water are joined the mixed of heat
In compound.Product be solid content be the clear light yellow solution of 40.0%.This is dispersant 10.
Embodiment 11
By 60 parts of polyisocyanate prepared by tetramethylolmethane and hexamethylene diisocyanate (
4,670, No. 068 United States Patent (USP) embodiments 1, have the degree of functionality of 4.5) and 0.02 part
NEOSTANN U-600 puts in reaction vessel, and at nitrogen and stirred at ambient temperature.
By 215.4 parts of PEG methyl ethers (MPEG-1000) by Dropping funnel with 1.5 hours time
Between be added dropwise in reactor.Reactant mixture is heated to 70 DEG C, and according to DIN
53185 by the reduction of titrimetry monitoring NCO%.When NCO% is down to 0.93%, will
2.1 parts of diethylenetriamines (DETA) were added dropwise over the time of 1 hour.Mixture is heated
To 85 DEG C and be stirred for 3 hours at such a temperature.Remove thermal source.416.28 parts of water are added
Enter in the mixture of heat.Product be solid content be the clear light yellow solution of 40.0%.This is
Dispersant 11.
Comparative examples
FX 365 is the wetting agent purchased from Elementis Specialties
FX 600 is the dispersant purchased from Elementis Specialties
Performance Evaluation
In order to disclose the performance of the dispersant described in embodiment 1-9, by by dispersant with table 1
In concentration add to 150mL vial, prepare the condensed pigment without binding agent.
Measure wetting effect and viscosity.
Table 1
DF 665 is the defoamer purchased from Elementis Specialties
DF 7620 is the defoamer purchased from Elementis Specialties
Zirconium (zicronium) pearl of mixture and 200 parts of a diameter of 2mm is merged.Also use
Carbon Black MA 100 and Heliogen Blue D 7079.With the pigment being loaded with 25%
Black pigment concentrate and the blue pigment concentrate of the pigment that is loaded with 30% prepare aqueous
Dispersant.
Vial is placed in Scandex disperser and inclusions is rocked grinding by vibration
Until particle diameter is less than 5 μm.Fineness is measured with fineness gauge.Use cone-plate several in range of shear rate
What structure measures the viscosity of dispersion liquid on Brookfield viscometer.Fineness and viscosity data exist
Shown in table 2 and table 3.
Table 2
Table 3
In the case of without departing substantially from the purport of the disclosure or essential attribute, the disclosure can be with other
Concrete form is implemented.Therefore, table should be carried out with reference to claims rather than aforementioned specification
Show the scope of the present disclosure.Although aforesaid description relates to the preferred embodiment of the disclosure, but
Should be noted that other change and amendment will be aobvious and easy to those skilled in the art
See, and can make in the case of without departing substantially from the spirit or scope of the disclosure.
Claims (15)
1. dispersant, it includes derived from following fragment:
(1) one or more have the polyisocyanate of at least 2 isocyanate groups,
(2) there is the monofunctional compound of isocyanate-reactive functional moiety；And
(3) amine degree of functionality is two or more polyamine.
Dispersant the most according to claim 1, wherein 50%-90% equivalent is described poly-
The isocyanate groups of isocyanates is combined with described monofunctional compound, and 10%-50% works as
The described isocyanate groups of amount is combined with described polyamine.
3. according to the dispersant according to any one of claim 1 and 2, wherein said simple function
Compound independently selected from aliphatic compound, alicyclic compound and aromatic compound, and
A combination thereof, described monofunctional compound has the molecular weight of 350 to 5000, and described single official
Can be contained at least one independently selected from following group by compound :-O-or-COO-and group thereof
Close.
Dispersant the most according to claim 3, wherein said isocyanate-reactive official's energy
Part is independently selected from hydroxyl, amine or imines and combinations thereof.
Dispersant the most according to claim 4, wherein said monofunctional compound is independently
Poly-(C selected from the ethylene oxide group containing 60%-99%2-4-alkylene oxide), polyester oligomer,
And combinations thereof.
Dispersant the most according to claim 5, wherein said polyester oligomer contains derivative
From dicarboxylic acids and the fragment of ethylene glycol.
7. according to the dispersant according to any one of claim 3 to 6, wherein said poly-isocyanide
Acid esters is diisocyanate, and it is independently selected from toluene di-isocyanate(TDI), isophorone two isocyanide
Acid esters (IPDI), hexamethylene diisocyanate, diphenyl-methane-4,4'-diisocyanate, bicyclo-
Hexyl methane-4,4'-diisocyanate, 1,4-double (2-isocyano-2-base) benzene, trimethyl six methylene
Group diisocyanate, or the mixture of these diisocyanate.
8. according to the dispersant according to any one of claim 3 to 6, wherein said poly-isocyanide
Acid esters is independently selected from isocyanate adduct, isocyanates biuret, isocyanates isocyanide urea
Acid esters or the mixture of this kind of polyisocyanate.
9. according to the dispersant according to any one of claim 7 or 8, wherein said poly-isocyanide
Acid esters is independently selected from toluene di-isocyanate(TDI) and trimethylolpropane adduct, hexa-methylene two
Isocyanates biuret trimer, hexamethylene diisocyanate isocyanurate trimer, different
Isophorone diisocyanate isocyanurate trimer, hexamethylene diisocyanate isocyanuric acid
Ester trimer, and isophorone diisocyanate isocyanurate trimer.
10. according to the dispersant according to any one of claim 3 to 9, wherein said polyamine
Independently selected from polymine (PEI), polyvinylamine, polyallyl amine oligomer, ethylene Asia
Amine oligomer, and combinations thereof.
11. dispersants according to claim 10, wherein said polyamine independently selected from
Diethylenetriamines (DETA), trien (TETA), tetren (TEPA),
Penten (PEHA), six ethylidene seven amine (HEHA) and combinations thereof.
12. according to the dispersant according to any one of claim 3 to 11, wherein said point
Powder is water miscible.
13. according to the preparation method of the dispersant according to any one of claim 1 to 12,
Wherein said polyisocyanate and described monofunctional compound are reacted to form isocyanates list adduction
Intermediate.
The preparation method of 14. dispersants according to claim 13, wherein said isocyanide
Acid esters list adduction intermediate and described polyamine are reacted to form described dispersant.
15. dispersions, it comprises (i) independently selected from organic pigment solid, inorganic pigment solid
And combinations thereof pigment, (ii) polar liquid medium, and (iii) is according in claim 3 to 12
Dispersant described in any one.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2014/001051 WO2016082058A1 (en) | 2014-11-25 | 2014-11-25 | Urethane dispersants |
| CNPCT/CN2014/001051 | 2014-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106146796A true CN106146796A (en) | 2016-11-23 |
Family
ID=56073271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510144172.0A Pending CN106146796A (en) | 2014-11-25 | 2015-03-30 | Urethanes dispersant |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP3046661A4 (en) |
| CN (1) | CN106146796A (en) |
| WO (1) | WO2016082058A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109880038A (en) * | 2019-03-05 | 2019-06-14 | 广州浦利姆环保科技有限公司 | Aqueous polyurethane and preparation method thereof, aqueous color paste |
| CN112724349A (en) * | 2019-10-28 | 2021-04-30 | 立邦涂料（中国）有限公司 | Novel polymers and uses thereof |
| CN113631671A (en) * | 2019-03-12 | 2021-11-09 | 亨斯迈石油化学有限责任公司 | Dispersants prepared from isocyanates and amines |
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| US4929705A (en) * | 1988-03-30 | 1990-05-29 | Bayer Aktiengesellschaft | New polyisocyanate-polyaddition compounds, a process for their preparation and their use for the dispersion of solids |
| US5910556A (en) * | 1996-08-30 | 1999-06-08 | Bayer Aktiengesellschaft | Dispersing agents for aqueous coatings compositions |
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| CN109880038A (en) * | 2019-03-05 | 2019-06-14 | 广州浦利姆环保科技有限公司 | Aqueous polyurethane and preparation method thereof, aqueous color paste |
| CN109880038B (en) * | 2019-03-05 | 2021-09-28 | 广州浦利姆环保科技有限公司 | Waterborne polyurethane, preparation method thereof and waterborne color paste |
| CN113631671A (en) * | 2019-03-12 | 2021-11-09 | 亨斯迈石油化学有限责任公司 | Dispersants prepared from isocyanates and amines |
| CN113631671B (en) * | 2019-03-12 | 2022-10-21 | 亨斯迈石油化学有限责任公司 | Dispersants prepared from isocyanates and amines |
| CN112724349A (en) * | 2019-10-28 | 2021-04-30 | 立邦涂料（中国）有限公司 | Novel polymers and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3046661A1 (en) | 2016-07-27 |
| EP3046661A4 (en) | 2016-10-12 |
| WO2016082058A1 (en) | 2016-06-02 |
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